Date Night
by jhoom
Summary: Castiel plans a romantic dinner date with Dean to celebrate their two month anniversary. Of course Cas' plans go completely out the window once Dean takes over... (continuation of my story Welcome to SKU)
1. Chapter 1

**AN:** I'm back! This is my little continuation of Welcome To SKU. It's the second installment in this verse and follows pretty much directly after the events of the first story. That being said, you probably don't need to have read the first part to get the gist of what's going on here. I'm going to try and avoid doing too much exposition about how things have been going since the end of pledge week - I'll give an idea of what the boys have been up to, but I'm not going to spell it out.

Once again, these two defied my expectations. I figured I'd have the main sex stuff at the end, just a bit of build up in between... aaaand then Dean had other ideas. Whoops? I guess I'm not used to writing horny college students? Cuz the adults I write can generally keep it in their pants for a lot longer... So basically, this was supposed to be one chapter, and I had to break it up into two.

The second chapter is planned out, I just gotta find time to sit down and write it...

Come visit me on tumblr at jhoomwrites - I'm always up for distractions :)

* * *

It's stupid. Cas knows damn well that it's stupid. It's the type of romantic, lovey dovey nonsense he used to make fun of in high school. Yet here he is, planning a fucking two month anniversary date. The type of shit that teenagers did right before they broke up a week later.

Un-fucking-believable.

Of course, things aren't that simple. If it were merely an obnoxious gesture to show off how _awesome_ things are, Castiel wouldn't bother. Because things _are_ awesome and he doesn't need the validation in the form of acknowledging the ridiculously meaningless passing of a scant two months. And yes, he's ranted about this to his friends on multiple occasions as they watched yet another doe-eyed couple profess their undying love to each other in the form of stuffed teddy bears and a half dozen roses.

Castiel swore to himself that he'd never be _that guy_.

And here he is, being _that guy_.

He thanks the hostess and hangs up the phone, circling the date and time of his reservation about five times. Sighing, he throws down the pencil and tries not to sulk.

In all honestly, the date's not so much about the anniversary. He's pretty sure if he said, "Happy two month anniversary!" to Dean, all he'd get would be a fist bump and a peck on the cheek. Or possibly a raised eyebrow about how he's been counting the time.

(He hasn't, okay? It's just that he _happens_ to know the date they first officially hooked up because it was the end of pledge week. And he just _happened_ to remember that little tidbit as he started an essay, one that _may_ be due on their two month anniversary. So sue him.)

But Dean, well into his junior year, is running himself ragged trying to keep up with his coursework. Even his physics and math professors - by far his favorite and easiest courses - are piling on so much work that Dean can hardly keep up. He wouldn't even sleep at night if it weren't for Cas forcing him to bed before he passed out as his desk.

So basically, Castiel justifies the sappy idea of a two month anniversary celebration with the excuse of Dean's mental health. Which, all in all, is a pretty damn good excuse.

Reservation on the books, all he has to do is bring it up to Dean. They don't see each other until that evening. Cas has a late study group on Mondays, but luckily the frat house is close to the coffee shop his classmates like to meet in. Since he'd have to pass by it on the way to his dorm, he usually stops by. More often than not, he spends the night too.

Sitting against the headboard and building up a comfy pillow fort, Cas props up his laptop and Spanish notebook. As he flips through to find his notes on the subjunctive, Cas passes by the post-it note reminding him to talk to Dean about dinner.

"Dean?"

The older boy doesn't react, keeps chewing on his pen and staring over the brim of his glasses at a textbook (and _fuck_ \- the first time he saw Dean wearing honest to god _glasses_ , Cas pushed him against the nearest wall and blew him right then and there).

"Dean?" He waits, then tries a third time while stretching out across the bed to tap him with his foot. "Dean?"

"Mmmm?" is the only response he gets.

Sighing, Cas decides that's the best he's going to get right now. "So, uh, this Friday is our two month anniversary and I thought you'd like to go out to dinner."

"Dinner? Yeah, yeah that sounds good."

Okay, the fact that Dean hasn't called him out on the two month thing makes him think he's at best only half listening. Cas can work with that. "Okay, well... I made reservations for seven at the Charleston. I can get your suit dry cleaned if you need me too and we can... What?"

Dean has completely abandoned his studies and is starring at Castiel intently. "The Charleston's the nicest place in town."

"Yeah, I know," he says slowly, trying to decipher what Dean's really saying. "I yelped it to find the best one."

"It's like... really fucking fancy. Suit fancy."

"I know, that's why I'm getting our suits dry cleaned."

There's a bit of heat behind Dean's eyes as he licks his lips and appraises Cas. "Bet you look damn good in a suit." Though the underlying meaning seems to imply his interests lie in getting him _out_ of the suit. "What's the occasion?"

Cas frowns but can't say he's all that surprised that Dean wasn't listening. "We've been dating two months. I thought it'd be nice to celebrate. Plus you could use a break. You're one night away from muttering differential equations in your sleep."

"I don't already do that?" he asks skeptically. "I have fucking nightmares about this shit."

"Is the nightmare that you're not allowed to solve more of them?"

He wads up a piece of paper and throws it at Cas. "Fuck you."

Cas swats the paper aside, knocking it onto the floor. "Only if you're good."

He's only teasing, but Dean sits up a little straighter. "Oh yeah? Isn't it usually the other way around?"

And great, now _he's_ getting hard. God damn Dean Winchester and his total control over Cas' libido. He shifts a bit on the bed to try and give his growing erection more room. Dean doesn't turn to watch, but he does smirk knowingly.

"So you're good for this Friday?"

"Fuck yeah, I'm in." Cas is lulled by the dazzling smile into thinking that's it, they can go back to studying. "I've got some, uh, _conditions_ though."

He recognizes that tone of voice. He's intimately acquainted with the authoritative air that Dean can assume at the drop of a hat. Which is totally not helping the situation in his pants. Dean's been so busy lately (and it's not like Castiel hasn't had his own fair share of work) that they haven't done more than make out and maybe exchange handjobs before class.

Swallowing thickly, Adam's apple bobbing under Dean's attentive gaze, he clears his throat and asks, "And what might those be?"

Dean laughs and leans back in his hair, the picture of relaxed composure. The total fucking opposite of how Cas feels right now. "For starters, I'm picking out your outfit. I know you got a suit, but I want final say on the tie and shirt and all that."

That's... a bit of a let down, actually. He likes the idea of Dean choosing his clothes, but compared to the ways Dean _usually_ exerts his authority over Castiel, it's rather...

Well, it's boring.

How can things be boring already, it's only been two months?

"Easy enough," he hedges, because he doesn't want Dean to pick up on the tinge of disappointment he tries to suppress.

Dean smiles easily, not at all noticing Cas' tightened expression. Turning back to his notes, Dean adds almost as an afterthought, "And it goes without saying that you're not going to come between now and Friday night."

He chokes on nothing. His mouth opens and closes uselessly a couple of times as he struggles to find words. In the end, there are only two words that ever need to be said to something like that.

"Yes, sir."

The rest of the week is a struggle.

And fuck Dean, honestly. Because the ass now makes an effort to sexually frustrate Cas at every opportunity. The past few weeks there wasn't much in the way of sex, but it was fine when they'd been too busy to think about it. But every damn day, Dean finds a new way to torment Cas.

First it's just simple things like the exaggerated sway of his hips when he walks by Dean. Or his switch to sleeping naked instead of in his boxers and a shirt. Ugh, and then there's the incident with the popsicle on Wednesday afternoon. That actually attracts a fair amount of attention as they walk to class together, Dean's tongue darting out far more often than necessary and deep throating the cold treat like a champ.

All of that Castiel could easily survive. At some point, Dean figures that out and ups his game.

Thursday morning he wakes up to the whole bed shaking as Dean vigorously jerks himself off. He blinks a few times, convinced he must be dreaming, but then Dean moans and bucks into his hand and nope this is definitely happening.

"This isn't fair, Dean," he grumbles.

Dean smiled at him as he comes on his stomach. Cas rolls over and huffs angrily, his morning wood as annoyed about the whole situation as he is.

That evening doesn't go much better. After eating dinner with the other Sigma Sigma Beta brothers, they head upstairs. Cas has every intention of going to bed early. Not because he's tired, mind you, but the sooner he goes to sleep the sooner he can start tomorrow and get to whatever Dean has planned.

Of course, Dean's plans don't include Cas getting out of things so easily. He closes the door behind them and roughly drags Cas back against his body before he can get too far away.

"Where you going, Pretty Boy?"

Gasping at the old nickname, so rarely used now that they're dating, he doesn't resist as Dean pushes him back against the door. His hands go to Cas' waist, slipping under his t-shirt to run his thumbs along his skin. Bodies pressed together and a thigh slotted between Cas' legs, Dean hungrily nips at his lips before claiming him in a dominating kiss.

They didn't kiss during pledge week, and it didn't take long for Cas to learn that was probably for the best. He's always willing to submit to Dean - his gaze, his touch, his desires - but damn if the effect isn't compounded when Dean's owning his mouth with his tongue. Cas wraps his hands into the short tufts of Dean's hair, moans into the kiss and squeezes Dean's thigh tightly just so he has something to hold on to.

When Dean breaks the kiss, Cas leans forward to try and chase his lips. All his effort does is earn him a tsk and a firm grip on his hips. "Always so responsive for me." Dean ducks away from another kiss, goes in to whisper in his ear, "Turn around."

There's barely enough space to move with Dean so close, but he does as he's told, bracing himself against the door. There's maybe an inch between them, Cas' skin buzzing with the proximity but demanding more. Dean doesn't move in to fill the gap, so he turns to look over his shoulder only for his lips to be captured in another kiss.

He sighs in contentment, letting Dean set the pace for a kiss that's not as needy and demanding as before but certainly not chaste or innocent. Cas is vaguely aware of Dean's hands circling around to start undoing his pants. He lets Dean coax his hips into a better position to pull them down, but only so that his ass his exposed. Dean nudges his legs apart, though they can't go far with his jeans bunched up around his thighs.

"Good boy." And then Dean leans forward, lining up his body so that his cock was in the crack of Cas' ass. "Very good boy," he amends before starting to move. The door bangs against the frame every few thrusts and Cas hisses out, "Dean, they'll- they'll hear-"

"I don't give a fuck," he growls back. "Let them know you're mine."

All Cas does is whimper in response, biting his lip to keep other noises from escaping. "You like being mine, don't you Cas? Like letting me use you like this?"

"Yes, sir! I love when you use me-"

"You still don't get to come," Dean warns as his pace picks up. "You're- Fuck..." And then the rhythm picks up and he loses the ability to speak. Cas holds on, in for the ride. He does his best to ignore the sensations and heat running through him so he can follow Dean's order not to come. The chafing of denim against his bare skin help keep him grounded (but fuck even _that's_ enjoyable, the harsh drag of Dean's clothed cock against his exposed hole).

Soon Dean moans a strangled cry into the back of Cas' neck and then goes stock still, his weight pinning Castiel to the door. It takes a moment for him to register what just happened.

"Did you seriously just come in your pants?"

Laughing breathlessly, Dean shrugs and starts to stand back up. "Sorry, babe. Just a little worked up thinking about tomorrow."

"Big plans?" His mouth waters in anticipation. He's spent the entire week wondering what Dean's going to do to him tomorrow night after dinner. It's been torture, and it'll be even worse sitting at that nice restaurant with him, having to watch as Dean calmly enjoys his meal while Cas fidgets and tries not to beg to leave early.

"Fuck yeah."

"You know, since _I'm_ the one whose idea it was, shouldn't I get to-"

"Nope." His grin turns into a wince pretty quickly when he starts moving towards the bed. "Ugh, I need to get out of these clothes."

With willpower that Dean's always so keen on testing, Castiel ignores his own aching dick and tries to get a handle on his arousal. Because apparently he's got to pivot from being used as a sex toy to studying fucking economics without even getting to come.

Fuck his life.

Fuck fucking his life. His life is awesome.

* * *

 **AN:** I know Cas thinks the two month anniversary thing is kinda lame, but I personally think it can be cute. (Honestly... me and my bf barely celebrate our anniversary except as an excuse to grab a nice dinner...)

Also Cas, you should not be underestimating Dean by thinking things will be *boring*.


	2. Chapter 2

**AN:** Ahahahaha did I say two chapters? Because I obviously meant three... The actual date (and smut) that's the whole basis for this installment will be next chapter :)

Thanks to sly for beta reading for me and dealing with my continuing struggles with tense confusion

* * *

Dean unceremoniously kicks him out of the frat house early the next morning (though thankfully without testing Cas' willpower with further displays of Dean getting himself off).

"I'll pick you up at your dorm. I'll have someone drop off what I want you to wear with your charcoal suit."

He eyes Dean suspiciously. "How do you know my suit's charcoal?"

Dean just laughs like it's the dumbest question he's ever heard. "Dude, I've been in your dorm room. Didn't think I'd snoop around?"

With that in mind, the whole walk to class Castiel wonders if he did a good enough job hiding his dildo and porn collection. He doubts it - not because they're not discreetly put away, but because given the opportunity to poke around, it's unlikely Dean wouldn't have uncovered _everything_. The suit was in the back of his closet in a garment bag and he'd been curious enough to look in there, meaning he'd have no qualms about looking anywhere else.

Hell, he probably cataloged all of the stuff his roommate Inias has, too.

His classes are a nightmare. They're by no means difficult. There are no tests today, no upcoming projects to worry about, and (most surprisingly of all) no homework over the weekend that he hasn't already taken care of. It should be the easiest day he could hope for. And it would be, if he weren't so damn _curious_ about what Dean planned for the evening.

(And yeah, maybe it should bother him that Dean's usurped his date night idea and made it completely his own. But he knows damn well that Dean'll take care of him, so it's kind of hard to be too upset.)

Anticipation builds all day, makes it impossible for him to eat at lunch. Which, as Kevin points out when Cas generously gives him his fries, is probably a good thing.

"Fancy restaurants are expensive, wouldn't want to go on a full stomach." Kevin shrugs and talks around a mouthful of fries. "May as well get your money's worth."

He gets back to his dorm room around four and tries to do some reading. He re-reads the same damn paragraph three times before he determines it's a useless venture. He's tempted to jerk off just to release some tension (and yeah, maybe part of the appeal is it would force Dean to punish him for deliberately disobeying him), but he's gotten so used to not being allowed to come. The build up is part of what he craves and he doesn't want to ruin the moment when he _finally_ gets permission.

That of course means there's _nothing_ for him to do until Dean picks him up around 6:30. He's got another _two hours_ of down time and not a damn thing to focus on-

The Harry Potter theme is rapped onto the outside of his door. Cas stops pacing (when did he even _start_? god he's a mess) and rushes to answer the door.

"Inias, did you forget your key-"

"Definitely not Inias, but hey!" Charlie grabs his hand, shakes it enthusiastically and then ducks by him into the room. Not sure what prompted the unexpected visit, Cas squints at her in confusion and remains frozen with his hand on the door knob.

"You guys _really_ need to spruce up the place. I mean, seriously, not a _single_ poster? I get the whole less is more thing, but this is _college_. Your one chance to decorate your room in obnoxious posters without anyone judging you - I mean, unless your choice in poster is lacking, then they're _totally_ gonna judge - and all you have is-" She leans forward to squint at the papers tapped above Cas' desk. "Dude, is this your class schedule and syllabi? What the fuck man, you a robot or something?"

"I... don't have any posters?" And though he feels he shouldn't need to defend his (or Inias', for that matter) decorating choices, there's something of an apology in the way he says it.

"Oh, sweetie." And she looks genuinely sad about that, like it's a tragedy against mankind as a whole that Castiel Novak doesn't have a single poster to his name. "I'll take care of it," she says with confident smile that offers no room for argument.

"Charlie, I appreciate the offer, but you really don't have to do that. I don't really spend a lot of time in here-"

"I'll bet you don't." The exaggerated eyebrow waggle makes him blush despite himself, so he gives up. His experience with Charlie makes him think he'd give in eventually, so why put up the fight?

"Did you only come to question my taste in room decor?" he asks dryly.

" _That_ was just a fortuitous turn of events. No, I'm here to drop this off." She lifts up a giant box (how the *hell* did he not notice it before) and holds it out to him. Finally abandoning his post at the door, he walks forward and hesitantly accepts it. "Dean-o wanted me to drop it off, and since I kinda owe him for bailing me out of an awkward situation with an overzealous co-ed a few weeks ago, I was only too happy to oblige."

"What happened?" he asks, voice thick with concern.

She shrugs, red hair falling from her shoulders. "Stole his girlfriend. Didn't take too kindly to it."

The box is a simple white cardboard. Every seam is sealed with tape, Dean's neat handwriting all over it. Block letters read, **DO NOT ACCEPT IF OPENED. I REPEAT, MORE DIRECTLY SO THAT THE PEANUT GALLERY UNDERSTANDS: CHARLIE BRADBURY, DO NOT OPEN THIS BOX OR WE'RE NOT FRIENDS ANYMORE.**

He takes the box and eyes her suspiciously while he inspects the outside. "It appears to still be intact."

Charlie rolls her eyes and huffs dramatically. "I ONCE ate a piece of pie from a box labeled PROPERTY OF DEAN WINCHESTER DO NOT EAT UPON PENALTY OF DEATH, and suddenly _I'm_ the ridiculous one."

"Charlie."

"Alright alright, geez. Enough with the third degree. So I would've _totally_ peaked, but I wouldn't have said a damn thing. Dean's all tight-lipped about this kinda stuff, except that he's crazy about you, and me and Jo are _dying_ to know _anything_."

He tries his best to suppress the stupid grin trying to form. Dean's crazy about him. _Him._ I mean, he _suspected_ and Dean's said as much, but it's nice to hear it from another source. "Thank you, Charlie."

"That's it? No juicy deets about this date night?" When Castiel remains stoically silent, she crosses her arms and glares at him. "I see how it is. But don't think I'm going to let this drop, Novak."

"It never occurred to me."

Charlie punches his shoulder on the way out. "You two kiddos have fun tonight!" she calls as she disappears into the hallway, shutting the door behind her.

It takes a few moments for Castiel to process the whole exchange, but then he's eagerly rushing to his desk to grab a pair of scissors. He forces himself to slow down and carefully cut through the tape. The box is surprisingly heavy for something that should only contain a shirt and tie, and he doubts Dean would've gone through the trouble of scaring off Charlie if it were something so bland.

(Although...)

When he pries open the top, he sees a note folded on top of a bunch of items, each individually wrapped in tissue paper. Cas moves to his bed, putting the box in the center and focusing on the note.

 _Here's your outfit for the evening. I'm gonna need you to wear **all** of it - I'll be checking. Make sure you're waiting out front for me. I want everyone to see how fucking hot my boyfriend is. _

_Charcoal suit, brown shoes, brown belt. No hair product, you look fucking hot with the messy 'I just got fucked by my boyfriend' look you're usually working._

 _See you soon,_

 _Dean_

 _P.S. Still not allowed to come._

He squints down at the box. There's... a lot of items in there, and he wonders what exactly Dean's stuffed in there. He takes them all out, not opening them up yet, just to see how much there is.

Five. Five mystery items, all of which he'll need to wear this evening. Some are obvious, so he starts with them to prolong the suspense. The first is a plain white button down shirt. Completely unnecessary, since it's not like he doesn't have his own. But it's no doubt Dean's, and Dean has always had a thing for seeing Cas wearing his clothes. Especially in public.

Putting the shirt aside, he reaches for the next most obvious bundle. Much smaller but also plumper, he rips through the tissue paper to find a sapphire blue tie. At first he thinks it's a close match to his eye color, but when the light reflects off it, it seems more that it's _similar_ enough to invite the comparison yet different enough that it'll bring out the blueness of his eyes.

His heart beats a little faster and affection swells through him. He grabs the closest bundle just to distract himself from the feeling. It's the smallest, though not by much, and inside he finds a blue pocket square. It's silk in a muted orange. No doubt something to give just a pop of color but without drawing too much attention. Fuck, he doesn't even know how to use pocket squares. Now he's going to have to look that up.

(He internally thanks Dean for providing him another distraction, otherwise he'd go crazy before dinner.)

Only two left to choose from - the ominously square one, heavier than the rest, and the one that looked similar to the pocket square in size and shape. He briefly considers before reaching for the small one.

The weight and feel makes it obvious that it's more clothing, though he has no idea what else there could possibly be. He suspected earlier that there might be cuff links, but that doesn't seem to be the case. So what on earth did Dean-

Oh.

 _Oh._

The satiny panties, a deep blue that's about two shades darker than the tie, have orange lace frills that go perfectly with the pocket square. The satiny material seems to have a bit of stretch to it, which is good because they seem like they're at least a size too small. Maybe that's just in comparison to the boxer briefs he's used to.

It's not what he expected - and really, he had no idea what he _was_ expecting - but the idea that Dean _picked these out_ for him... Found a matching tie and pocket square, thought about every single detail-

Great, now he's hard and hours away from any sort of relief on that front.

The last item remains untouched. It's clearly a box, the angular shape taunting him from beneath the tissue paper. His fingers twitch with the desire to open it, but he hesitates to drag the moment out a little longer. Slowly, he rips through the tape that's keeping the paper together, pulls off the sheet and doesn't let his eyes focus on the box until it's completely revealed.

A butt plug. Which... okay, he's not going to turn it down, but Dean already got him one when they first started going out. (Well, first started fucking. Technically the dating part came a few days after.) Frowning in confusion, he turns the box over to read what exactly made Dean purchase him another-

 _Vibrating Anal Pleasure Butt Plug_

"Well played," he breathes out. His mistake for underestimating Dean. How he managed to become so complacent in only two months is a bit of a mystery, but he's willing to admit he was wrong.

Upon further investigation, it appears the box has already been opened. Just to be thorough, he checks anyway, but isn't surprised that the remote is missing.

Yeah, no way his erection's going down any time soon.

With a little over an hour before he needs to be outside to meet Dean, Cas busies himself getting ready. He takes a long, thorough shower. He avoids his cock altogether, worried about where the temptation might lead, and sticks to scrubbing the rest of himself from the roots of his hair to the tips of his toes.

He dries off as quickly as he can and mentally thanks Inias for being out of town this weekend to visit his sister, because now he has to go through the process of getting dressed. Starting with opening himself up and working in the vibrator.

And yeah, okay, he started that job in the shower. But it still takes a good amount of time to stretch himself enough to accommodate the plug. Mostly because he has to ease up often to avoid getting any more worked up. He's probably going to be semi-hard for the next few hours no matter what, but fuck if that means he's going to let himself stay fully hard the whole damn night if he can help it.

(Grazing his prostate doesn't help matters, but when the plug finally slips in it nestles itself against the nerve bundle. Probably what Dean would want, anyway, so he leaves it there.)

Next come the panties. And wow, that's something he never thought he'd try, but here he is slipping them on. They're a little snug and it takes a moment to adjust his dick comfortably, but once in place they feel pretty nice. Like... _really_ nice. Especially when he puts on his dress slacks, zipper and belt holding the soft material flush against his skin. He could definitely get used to this.

The rest is relatively straightforward. He's not great at tying ties (he so rarely has occasion to dress up like this), but he does what he hopes is a passable half Windsor. The pocket square takes a few tries, and a few YouTube videos worth of advice. Despite the apparently wide array of options for folds, he goes with a very basic one that leaves a crisp line of orange peeking out of the pocket.

Cas admires himself in the mirror. He wishes he could see the panties hidden underneath, but each step he takes reminds him of the other two items he's wearing. The slight discomfort of the plug meshes so well with the drag of satin over his ass and cock. It's _amazing_.

The only down side of this ensemble is that his pants hide _nothing_. Not his runner's thighs, not his toned ass, and certainly not his half hard dick vying for his attention. He forces himself to breathe deeply and relax, or at least to calm down enough that his constant state of arousal isn't immediately apparent to anyone who happens to look. By sheer willpower alone, he keeps his mind resolutely blank as he grabs his wallet and heads downstairs to wait for Dean.

He takes the steps two at a time, trying to imagine which will be more fun - dinner itself, or whatever Dean's got in mind for _after_.


	3. Chapter 3

**AN:** Yeessssss I planned out a short sequel to something and IT STAYED SHORT. (I'm totally ignoring that this was just supposed to be one chapter but got a bit longer... and then I added a timestamp...) This is just fun, sexy nonsense to follow up on the fun, sexy nonsense (with feels) from the original. The next installment will be longer than this one and will focus more on the feels aspect and be a little bit of a downer... but there'll still be smut, so there's that I guess? If you're interested in seeing more of the series, make sure you subscribe to the series South Kansas University or you'll miss out :)

Check me out on tumblr and feel free to give me suggestions about things you might like to see in this series (I do have the next two installments pretty much planned out, have a general idea for a third one after that, but otherwise I have no clue what I'd do).

* * *

Castiel is only left waiting for ten minutes before Dean shows up. Some of the other students from his hallway wave or say hi on their ways in and out, and one of the girls even gives him a once over and a wink. None of the ones who give him an appreciating look bother to flirt, though. They've seen Dean around enough to know Cas is taken.

The Impala pulls up to the curb, the engine's gentle rumble garnering a few curious looks and whispered comments of appreciation. Cas flushes on Dean's behalf, knowing full well the older boy would be pleased at the praise and attention his baby is receiving from his dorm mates. The car is his pride and joy, a graduation gift from his father that he maintains with the love and care one would not normally bestow upon an inanimate object.

(He also smiles at the memories he has of Dean, hands in his pocket as he awkwardly looks at the ground and shuffles his feet, when he's asked Cas to do a repeat of pledge week and wash the car. Each time he's humored Dean. Striped down to just a pair of shorts and soaped up the car, scrubbing it from top to bottom while Dean looks on with obvious hunger.)

(And okay, there was the one time he got a glimpse of Dean doing the same. All wet and bent over the hood, remarkably short shorts tracing the curves of his ass... He got the appeal, he really did.)

He doesn't want to look too eager. He hesitates a moment before pushing off from the dorm wall and walking over. The somewhat awkward way he has to move to accommodate the plug keeps him from jumping up, forces his movements to be measured and precise as he walks over and gets in the car.

The fading light cast a glare on the windows that made seeing inside near impossible, but now as soon as he opens the door, he's greeted by Dean's smile. He holds Dean's gaze as he slips into the passenger seat. He has a perfect view of Dean watching carefully as he gingerly seats himself. There's something predatory about it, and soon Cas pinpoints why. He's not sure what gives it away - maybe he hisses slightly or winces when he makes contact - but Dean's eyes darken for a second. His tongue darts out to lick his lips, and his smile changes from warm to smug in an instant.

Dean waits until Castiel has closed the car door before saying, "I see you followed my directions, Pretty Boy."

"Of course, sir."

Satisfied, Dean shifts the car into drive and starts heading off campus. The restaurant isn't far, but the ride is long enough that it should warrant conversation. It doesn't. Castiel is abuzz with anticipation, unable to voice any of the thoughts running through his head. He has no idea what keeps Dean quiet, but he's glad for it. He's not sure he has the brain power for conversation at the moment.

The strange tension almost immediately dissipates when they arrive at the restaurant. Dean lets the valet take his keys (with only a minimal amount of threatening glares) then walks around to open the door for Cas. Accepting Dean's outstretched hand, he finally gets the chance to look at his boyfriend's outfit.

His suit is a lighter gray than his own, a light blue dress shirt with an orange tie that matches his own pocket square. Dean's pocket square is a plain white, though with a three point fold that Castiel hadn't been able to get quite right when he tried. He's only ever seen Dean in a suit once before, back before they started dating, and this is a far cry from that. Although he'd looked good, then it was more like he'd thrown the outfit on because he needed to. Today, it's obvious the care he took in choosing it.

And he looks, well-

"You look very handsome, Dean." The word he wants to say was 'beautiful', but he changes it at the last second. Dean always shies away from such compliments, especially in public, and he doesn't want to embarrass him.

"Thanks," he says, and as Castiel predicted, a pink blush threatens to overtake his freckles. "You don't look so bad yourself."

Dean holds the restaurant door open for them, takes over at the hostess stand (despite the reservation being in Cas' name). It's the type of overly macho display that would normally irk Castiel... if it weren't for the underlying implications. The subtle control Dean's exerting to set the tone for the rest of the night.

Fuck it's hot.

As they're lead through the main dining area to their table by the large windows overlooking a nearby park, a spark of disappointment shoots through Castiel. He has no idea what Dean's plans entail, but he's spent a couple of nights this week _imagining_ the possibilities as he tried to fall asleep. And the idea of _maybe_ ducking under the table, hidden from view by the tablecloth, to unbutton Dean's pants and give him a quick blowjob while he enjoys his meal... Well, there's a certain appeal to that image.

No such luck on that fantasy. The dining room, though not full, has far too many couples and small groups for him to reasonably slip under the table un-noticed. Never mind that the tablecloths only hang a foot below the edge of the table, leaving their feet exposed.

(He puts the idea on the back burner, though. Something to pull out later when he wants to take care of Dean. Maybe Dean's birthday or Valentine's Day.)

(And great, now he's already making plans for future corny landmarks in their relationship. When he'd turn into such a sap?)

Dean, however, seems unbothered by the discovery. He flashes a smile to the hostess as he takes a seat and immediately starts perusing the menu. "Decent wine selection." He puts the drink menu aside in favor of looking at the entrees. "Too bad we're underage and I'm pretty sure I don't like wine. At least not enough for $15 a glass."

And just like that, they fall into easy conversation. They talk about classes, the frat's plans to hold a silent auction just before winter break, and the general nonsense that always seems to stem from any topic they bring up. If it weren't for the suits, it's exactly the way they'd be spending their evening in Dean's room.

In hindsight, it should be clear that Dean was lulling him into a false sense of security. Not on his guard, Cas falls for it easily.

When their server comes over to get their drink selection, Castiel gasps as he feels a gentle pulse from the vibrator.

"Are you alright, sir?" The server frowns in confusion. Dean does his best to hide a smirk.

"Yes. I'm- I'm fine, thank you." His voice is a little strained, but he still manages to order a.

When she disappears again, he half-heartedly kicks Dean under the table. Which of course earns him a higher setting on the vibrator.

"Oh _fuck_ ," he hisses through gritted teeth. Dean's smile is blinding as he lowers the setting to something more tolerable. "You're a terrible, terrible person."

"Me?" Dean asks in mock offense. "I think you mean I'm an awesome, thoughtful boyfriend. At least, I'm pretty sure that's what you meant, right?"

He grunts non-noncommittally.

It's a strain to not squirm, but he keeps himself focused on the conversation. Sure, he has to let Dean lead it, but he counts his ability to follow the thread of it as a victory. He doesn't want Dean to know how much it's affecting him. Make no mistake, it is. Dean doesn't need to know that. In this game of cat and mouse that they've fallen into, Castiel tries to make Dean work for his inevitable victory.

He sits stoically and endures his needy arousal. Which works out really well... Until Dean bumps up the setting again when the server drops off their drinks. He fidgets a bit but keeps any other reactions in check. When the server returns with their drinks, the vibrations kick up another notch. He has to bite his lip to keep from making a sound, though the concerned look he gets from the server shows his poker face is slipping just a bit.

They continue the meal like that. Each time the server reappears, Dean's hand discreetly disappears into his pocket to ratchet up the intensity of the vibrator. It's a slow, agonizing build up that has him leaking precome in his pants, but he grits and bears it. He doesn't want to give Dean the satisfaction of caving too soon.

Dean seems to have at least picked up on the fact that Cas is now beyond the point of passable conversation, so he fully takes over. It's getting more and more difficult to listen to Dean as he tells story after story. He's immensely proud that his hand only shakes a _little_ each time he brings up his fork to eat. There's sweat collecting on his brow and he has no choice but to occasionally shift in his seat. Not in comfort per se. It's more that his body is trying to find just the right angle to finish things off, even as his mind tries to will himself still and draw it out more.

By the time the entrees arrive, he's slowly undulating his hips back and forth. Not enough to be visible from a distance in the dim, romantic lighting of the restaurant. Hell, it's not even enough to take the edge off. But he honestly can't help it anymore.

"You're so fucking beautiful like this, you know that?" Castiel squints in confusion, not quite processing the words until a moment after they've been said. Dean's leaning toward him, voice low so it won't carry to the nearby tables. "Sitting there, takin' it like this is nothing. Hottest fucking thing I've seen, and that's saying something considering I've seen you marked up in my come." As an afterthought, Dean growls out, "Bet it'll be even hotter when I take you back to my room and strip you down, get a good look at you in those panties."

Castiel has remained quiet up to this point, swallowing every sound that threatened to escape as Dean eased him into tortuous bliss. Now he can't stop the whimper that Dean's words coax out of him. Dean's eyes dilate visibly, even in the candlelight. "I only got one more setting left - you think you can handle it?"

Usually Dean makes him voice his answers, but words are hovering out of reach. He nods frantically and hopes it'll be enough.

The vibration seems to double, though he knows that's impossible, and it rattles him a bit. He bucks up unmistakably and grinds back down hard. If the sudden movement drew the attention of the other patrons, he has no idea, lost to the uncomfortable pleasure. When his vision clears, he sees Dean watching him intently. He tries to smile, but his face won't quite cooperate and his expression's probably more in line with a grimace.

"You think you can come like this, Cas?" Dean asks, voice thick and an octave deeper than it was a moment ago. "Think you can come for me?"

"Am I-" Cas gasps as the movement forces the vibrator against his prostate. He wonders if he should move to try and edge it away, or if he'd rather ride out the feeling. Dean waits patiently as he re-collects himself, moves to ease up the pressure on his prostate so he can actually form words, and starts over. "Am I allowed to come, sir?"

"Fuck yeah." In his eagerness, Dean's voice is louder than it should be. Cas is pretty sure the woman at the nearest table glares at Dean's language, but no one else seems to mind. Dean rolls his eyes at the woman before turning back to Cas. Lowering his voice again, he whispers, "Yeah you can come, sweetheart."

Castiel might answer him, some babbled 'thank you' or maybe a wordless groan. Either way, he closes his eyes and leans back into vibrator and lets it pound against his prostate again. And... fuck, he's close. He hasn't come all week, no doubt because Dean's wanted this all along. Wanted to wind him up so much he'd be putty in his hands by the time he was actually allowed to come.

What finally sets Cas over the edge is when Dean's foot meets his under the table. He gently moves it up Cas' calf and then back down, repeating the back and forth motion a couple times. The contrasting intimacy sparks something in Castiel and he comes with a groan he muffles behind a clenched fist.

It takes him a while to come back down and re-orient himself. He takes in his surroundings, cataloging them in a detached way that almost feels like he's thinking about someone else. Soon, though, the boneless feeling recedes and he's able to sit up straight again.

Dean's smiling at his plate, resolutely ignoring him as he finishes up his steak.

To avoid suspicion (and to hopefully let the wet spot on his pants dry a little), Cas picks at his dinner a bit more. When he feels he's up to it, he excuses himself from the table and heads in the direction of the bathroom. Walking is a challenge. Between the orgasm induced high his body's still recovering from, the come sticking to him, and the butt plug (though he's now cognizant enough to realize Dean's turned off the vibrator), it's a miracle he makes it there without bumping into anything.

He gets a good look at himself in the mirror, and he's a mess. The come stain isn't all that bad, thankfully, but everything about him seems to scream that he just came in his pants at a fancy restaurant while his boyfriend mercilessly tortured him with a vibrator. Okay, so that's a little too specific, but he can read every bit of it in his reflection.

The bathroom is empty, but he won't chance getting caught with his pants literally down. He does his best to clean up the front of his pants. For good measure, he leans over to splash some cold water on his face. He hears the door open, silently praises his earlier decision not to unbutton his pants, and keeps trying to rinse away the sweat from earlier.

Hands wrap around him and the unmistakable feeling of a hard cock presses into him from behind. He jumps, which only pushes him back against Dean, who starts mouthing at his neck.

"Dean! What are you doing- We're in the _bathroom_ -"

"Shhh, don't worry baby," Dean coos as a hand snakes around and starts undoing Cas' pants. "I locked the door when I came in."

Okay, that's... that's actually a relief. It doesn't give them a whole lot of time, but it earns them at least some temporary privacy.

"Wanted to wait til we got back, but _fuck_ you got me so worked up." He keeps kissing Castiel's neck, nibbles at his earlobes. All a distraction as he pushes Cas' pants down. "So good for me, coming like that."

His pants slide down to his thighs. Dean doesn't even try to work them past his knees, just leaves them there and stares over his shoulder at the mirror. If Castiel thought he was a mess with his clothes _on_ , the effect is compounded without the pants. His panties are a mess, a huge stain of dried come marring the front of the blue fabric. Dean's fingers trace the lace and he hums appreciatively.

"So beautiful," he praises. His hands disappear and Cas can see Dean struggling to get his own pants out of the way. Dean wraps a hand around Cas' chest, pushing the tie over his shoulder as he goes, before pressing his fingers on Cas' lips. "Suck," he instructs, pushing three fingers in as soon as he opens his mouth.

Cas isn't sure what Dean has in mind, but he does as he's told. He lavishes each finger with his tongue as Dean jerks himself off. Soon Dean's pulling away and slicking up his cock with the spit. He nudges Cas's legs apart, then slips his cock between his thighs. Pressing his legs back together, Dean starts thrusting.

With nothing but stick and sweat to ease the way, Cas can't help but think there's too much friction, but Dean doesn't seem to mind. His brow is creased, a single minded determination to get himself off, and he keeps rocking in and out of the tight heat Castiel's body provides.

Dean's dick moves along Cas' perineum and teases at his balls through the fabric of the panties. Each thrust pulls them tight before easing up. Each shift of Dean's hips force the butt plug to move inside him. And Cas finds himself getting hard again. His erection's not as urgent as before, merely a sign of his interest instead of something demanding attention. He braces himself against the counter top and uses the mirror to watch Dean come apart.

"Was going to wait til I had you on my bed... Was gonna make you model that cute little outfit for me... strip down to your panties, pull them aside and fuck you hard," Dean pants in his ear. "Couldn't... couldn't wait that long."

Cas' only reply is to expose his neck, to offer the expanse of skin for Dean to lick and suck and _bite_. Dean, of course, is more than willing to accept. And total sex mastermind that he is, he waits until one particularly hard bite before turning the vibrator back on to full power.

"Ah! Dean-"

"Shhh," Dean hushes him. Puts his fingers back in his mouth for him to suck on, to swallow up all the noises he's starting to make. And yeah, maybe he didn't think he could come again so soon, but Dean's doing his best to get him there. "Gonna take care of you, baby, gonna make you come again in your pretty blue panties."

"Yes... yes, sir, please..." he struggles to speak around the fingers in his mouth, but he doesn't fight them, knows it's the only thing keeping him from screaming. His cock strains against the satin. Dean's free hand comes around to cup it, pulling the material tight as he strokes him just a half beat off from his own rhythm. "Please, sir, may I- May I-"

" _Yes_. God, yes."

Dean comes first, spilling himself between Cas' thighs. Come dampens the bottom of his panties, drips down his legs. Castiel doesn't last much longer, his dick pulsing against Dean's hand. Dean briefly sinks his weight into Castiel, humming in contentment as his hands move to snuggle Castiel close.

"That as awesome," he sighs.

"You ruined my panties, Dean."

"'s okay, I'll get you more." Dean breathes in his scent, then pushes away. "C'mon, let's go eat dessert."

They laugh and then hurry to clean themselves up. Who knows if anyone heard them - nothing they can do about that now, anyway - but they've pushed their luck staying this long. Except for the barely there flush on his cheeks, Dean looks no worse for wear. He gives Cas a wink before unlocking the door and dipping back out into the restaurant.

Castiel, on the other hand, is even more of a mess. He grabs some damp paper towels and disappears into one of the stalls. The lighting's no good, but he's too nervous about being interrupted to stay by the sinks. He does the best he can, but he ends up taking off the panties. Bunching them up, he contemplates how he can slip them into Dean's pocket without anyone noticing. It might be a small way to get revenge, but he has no doubt it'll get the reaction he wants.

(Namely, getting pushed up against the door of Dean's room and fucked like there's no tomorrow.)

Best two month anniversary _ever_.


	4. Chapter 4

**AN:** Timestamp for the restaurant - what the poor waitresses were making of this whole situation :)

Just to be clear, this is werewolf Kate from 8.04 Bitten and 10.04 Paper Moon. Yes I had to look up her name to be able to write her in.

* * *

Kate isn't necessarily strapped for cash, but between tuition and books, it's nice to have a little something extra to go see a movie or something. It's the only reason she gets a job at the Charleston. And they only really need her a few nights a week, so it fits in perfectly with her class schedule. It's not like working at a chain restaurant or something, which can be a real slog sometimes. No, it's nice and clean and the clientele are either quiet older couples, business professionals, or small groups celebrating special occasions.

Which is kind of why it's such a shock when she sees her next table be seated. They don't fit in with the usual groups she sees come through. Young - her age young, which is about a decade younger than her regulars - and handsome. Like, _incredibly_ handsome. Forget how to speak and stare for while handsome. Wow.

 _Luckily I'm getting my staring in **now** before I make an ass of myself at the table._

She waits for them to get situated, read over the menus so she can answer their questions when she stops by to get their drink orders. As she hovers out of site by the kitchen entrance, Bela comes up behind her.

"I will give you $50 right now if you let me take that table."

"What? Why?"

"One word, three letters. Those boys are _hot_ and I don't have any tables in that section. I want to get a better look and don't mind taking an extra table to do it."

Kate tsks slightly. "Hon, they're here on a date. They're not going to be interested in what you're sellin'."

"I'm a _very_ good negotiator, I'm sure I could make something work." She smirks behind her perfect teeth, then frowns. "What makes you think they're on a date, anyway?"

"People are our age don't dress up like that and go to a restaurant like this if it's not a date."

"Well, that's vaguely disappointing." They stare a little longer, before Bela perks up a bit. "I think the brown haired one is my math TA."

"You _think_?"

Bela waves a hand dismissively. "I don't exactly go to class. I go take the tests and that's about it. I think that's him, though."

"How exactly do you pass the class?"

"I sleep with the professor."

She laughs but then stops short at the look Bela gives her. "You're not serious." Bela quirks an eyebrow and walks off. "You're not serious!" Kate hisses after her, but really, she's not so sure.

* * *

"How are the lovebirds? Any weakness I could exploit to get in on that or maybe work my way into a threesome?"

This time, Kate knows Bela is kidding. Most likely. "Nope, sorry. They seem really cute together." She frowns, looking back at the table, and adds, "Though the dark haired one seemed a little… nervous?"

"Probably because brown hair is out of his league."

"What?" she asks, jaw hanging open in total shock. If anything, she'd have thought it was the other way around.

"Oh, darling, I'm not saying the dark haired one isn't a 9/10 on the hotness scale. He most certainly is. He might even be inching towards a perfect 10 once he's a bit older." Kate rolls her eyes, knowing all too well Bela's interest in older men. (Huh, so maybe she _is_ sleeping with her math professor.) "But brown hair is a calculus TA at an engineering school. Boy's smart. And you saw the way he walked in. Total confidence. He's just a tad more put together. And black hair must know that."

"Bela, I think you're over-analyzing it."

"You have a better theory?"

"Well…" She hesitates, tries to come up with something more flattering for the dark haired boy. "Maybe this is their first date and he's just shy."

Bela inclines her head to the side as if considering the possibility. "Probably wondering if he's going to be putting out tonight," she says archly, and Kate is starting to think Bela says shit like that just to see her reaction. "Let me bring out their bread and get a better look."

* * *

"So?"

"Hmm?" Bela asks without looking up from her phone. She finishes her text message and pockets the phone with the practiced ease of someone who's on it far too often. "You're right. Black hair is definitely nervous about something. Kept fidgeting. Barely even noticed I was there."

She seems mildly offended by the last part, but her curiosity shows through more.

"Poor guy." Kate sympathizes with him, she really does. He's clearly a nervous wreck, barely holding it together, despite the brown haired boy's obvious attempts to keep things light. She crosses her fingers and hopes their date won't be a total disaster.

* * *

"Kate?"

"Yeah?" She's out of breath from dropping off food at one table and rushing to get in orders for another. Currently she has about a five minute window before she has to be anywhere, and dammit she's going to take advantage.

"Where are your dreamy hunks?"

"Huh?" Her head whips around and sure enough, both the dark haired and brown haired boys have disappeared. "Shit, where'd they go? Think they were looking for me?"

She looks around the restaurant as inconspicuously as possible and catches sight of the brown haired guy making his way quickly towards the bathroom. Her shoulders slump in relief. "Found one of them." And she nods that way to get Bela's attention.

Bela watches him duck into the bathroom and then turns to look back at Kate. "I don't know if that's a good thing."

"Why?" Concern starts growing again.

"Well, for presumably both of your boys to be disappearing into the bathroom, that means one of two things." Kate stares back in confusion as Bela waits for her to pick up on it. When she doesn't, Bela rolls her eyes. "Either dark haired boy finally snapped and had a break down. Or he's physically ill. Either way, brown hair is going to go take care of him."

"Oh." She frowns, because both options suck. Her heart goes out to the dark haired boy. He seems sweet. Awkward as hell, probably because he's under too much stress right now, but sweet.

* * *

"They've been gone like, ten minutes. I'm starting to worry."

"That they'll try to make a run for it without paying?"

"What? No. I'm worried that maybe the dark haired one is like hyperventilating or something. Maybe I should send one of the guys in to check-?"

"Kate, you're overreacting. Give them another five minutes at least, I'm sure it's fine."

* * *

"Okay, maybe now you can start panicking."

Kate glares at Bela but continues her short pacing by the kitchen. Because fuck, what do you do if your table disappears in the middle of dinner? Does she tell a manager what happened? Does she have dessert ready for when they come back or assume they've changed their minds and skip it?

She's about two seconds away from completely freaking out when the brown haired guy steps out of the bathroom. He looks maybe a little worse for wear, but he's definitely heading back to the table. Kate watches like a hawk as he takes a seat and grabs his discarded napkin, putting it back on his lap and smoothing it out as though nothing's amiss.

"Well he sure looks like the cat who caught the canary."

Ignoring Bela's commentary, Kate rushes over (well, she manages to keep it to a brisk walk but that still earns her a few looks).

"Could I interest you in dessert this evening?"

He gives her a lazy smile. "Absolutely."

"Tonight the chef has prepared a chocolate cheesecake, a tiramisu, and an apple pie."

"Man after my own heart. We'll take the pie, please."

She tries a friendly smile but it falls flat, her heart rate not quite back to normal yet. Despite the way Bela presses in close behind her as she goes into the kitchen to pick up the desserts, she pointedly ignores her.

* * *

By the time Kate's making her way back to the table, desserts in hand, the dark haired boy has returned. The brown haired one is leaning over the table to fix his tie, though in general he seems about three times as disheveled as before. His hair is matted down with sweat and his suit jacket is definitely more rumpled. She frowns in concern as she takes the last few steps.

"Apple pie with a caramel sauce and whipped cream." As she says it, she looks over the dark haired boy. Although his clothes and hair are a mess, there's a shy smile pulling at his lips. He's about ten times more relaxed than before, no more squirming in place. And he actually meets her eyes when he thanks her for the dessert.

Bela pretty much abandons a table to follow her out of the dining area, almost stepping on her ankles. Each click of her heels was a _tell me tell me tell me_. Finally out of sight, Kate shrugs. "I have no idea what happened, but dark hair is a mess but looks seriously chill compared to before."

There's a blank expression on Bela's face before she bursts out laughing. It's loud enough that Kate has to nudge her further away from the dining room and shake her a bit. "Jesus, Bela, what's _wrong_ with you."

Waving her hands to get Kate away from her, she giggles through her first attempts at speaking. Eventually she chokes out, "Oh c'mon, isn't it obvious? Dark hair had a mini freak out during dinner, escaped to the bathroom, where brown hair either blew him in one of the stalls to calm him down or lit up a joint for him."

Kate chokes on nothing before recovering. "Bela, that's… that's… _No_ , ugh, now I can't get the mental image out of my head-"

"You're welcome, then, because that is a tasty image."

"I hate you! How am I supposed to look them in the eyes when I'm thinking about them blowing each other in the bathroom?"

Bela's answering grin is nothing but pleased.

* * *

Kate waves the couple good-bye as she picks up the check from the table. They really are cute together, and even if she blushed furiously every time she checked up on them after Bela's teasing (which the brown haired one definitely picked up on, though he just seemed mildly amused by it), they were a good table.

… But she's glad they're leaving, because there's no way she'd survive another minute with them.

(Oh _god_ , what if she runs into them on campus?)

* * *

 **AN:** I guarantee you Bela goes to her calc class a lot more after this. Every time, she'll do her best to flirt with Dean, just to get a reaction out of him. It doesn't work, which just makes her try even harder :)


End file.
